Poll results: here's what I booked (and the exact logic behind it)

Hey {{first name | reader}},

Happy Monday — and thank you!

A few weeks ago I sent you my "I'm stuck" newsletter and asked you to vote on my return flight from Europe. You showed up in a big way: tons of replies, and some very strong opinions!

As promised, I took your votes into consideration. And the winner was clear:

✅ Option C: Air France's newer business class to Brazil + positioning flight home

Second place: KLM
Third place: Lufthansa First Class (the chaos option)

Today's post is about what matters more than my specific flight:

This is what booking with points looks like in real life. It's not "just find business class availability and click purchase." It's strategy, trade-offs, risk management… and a little bit of personality.

So here's what I booked — and the exact logic behind it.

I voted for the Air France "new biz to Rio" option too… but I didn't end up booking GIG.

I booked CDG → GRU (São Paulo) instead, mainly because the timing was perfect:

And I love a daytime long-haul when I'm flying a great product. If I'm finally trying Air France's newer business class, I don't want to sleep through it — I want to enjoy the whole experience: lounge, meal service, cabin vibes, the seat, the little details. Day flight = perfect.

There is a GRU → COR flight at 10pm, with GOL Linhas Aéreas.

Which means I can land in Brazil, clear whatever I need to clear, and still make it home the same night.

This means I don't have to spend the night in São Paulo, which was the thing I didn't like about this itinerary. Now it is just: land → connect → home.

That's the difference between a plan that looks good on paper and a plan that feels good in practice.

When people talk about points, it's usually framed like a math problem:

"What's the cheapest redemption?"

But if that's the only lens, you can miss the real value.

Points give you optionality.

They let you pick flights based on the experience you want — as long as you build the plan in a way that doesn't blow up your trip.

So yes, I picked the "avgeek" option. But I engineered it so it's still sane. And that's the game:

Make the fun option behave like the practical option.

Positioning flights are where people get burned. It's not because positioning is inherently bad — it's because people try to do it with tight timing and no backup plan.

Here's what I did differently:

1) I built the connection intentionally

I chose a routing where I'm not trying to connect on a razor-thin schedule. I have a same-night connection, yes, but it's not "land and sprint."

And I'm paying attention to the airport realities. GRU isn't a tiny regional airport. It has flights. Options. Hotels if needed. It's not ideal, but it's workable.

2) I picked a return flight with a built-in escape hatch

This part is the biggest lesson:

I booked GRU → COR in Premium Economy (it's GOL, so there's no business class cabin). It cost about 20% more than economy.

Why pay extra for Premium Economy when it is just an economy seat with a middle seat blocked? Because it came with free cancellation.

That means if my Air France flight is delayed in a way that makes the connection risky or impossible, I'm not trapped. I can cancel the GRU → COR ticket and get the money back.

That single decision turns a "positioning risk" into a "positioning inconvenience."

And that's exactly how you should think about positioning:

This wasn't the cheapest option.

I booked the Air France long-haul for ~85k miles + ~$400 in taxes.

Air France's newer business class has those bulkhead seats that people obsess over — and for good reason. The space is meaningfully better.

There was one bulkhead seat showing as empty.

And there was absolutely no chance I was going to:

So I paid $200 for seat selection and locked it in. I am not planning on taking this flight or flying this product again any time soon, so I better take it. Because my goal isn't to win the cheapest redemption (I would have gone with Air Europa if that was the case) — my goal is to get the trip I actually want, with the least stress possible.

Now, about the third-place finisher: the degenerate-gambler option.

Yes — I'm still going to monitor Lufthansa First Class space close-in. Because it is one of those bucket-list experiences that's genuinely worth rearranging a trip for… if it actually opens.

But here's what changed:

I'm not building my entire return around it.

I already have a great flight locked in. If First opens, it becomes a "bonus decision," not a "save-my-trip decision."

That's the difference between:

If it opens and the switch makes sense, I'll consider it.

If it doesn't, I'm not stuck in a mediocre product feeling regret. I'm still flying a great business class seat on a daytime flight (some people are calling it the best business class seat in the air, when talking about those bulkhead seats) — and getting home the same night.

If you remember one framework from this email, make it this:

When booking with points, ask yourself:

That's how you turn points from a hobby into a tool.

Thank you again for voting — you genuinely helped me make my mind!

More deals + strategies coming Wednesday.

Catch you in the clouds,

Tomi